Taking no risks is the biggest risk of all

For most of my life, I’ve always “played it safe.” I went to college, majored in something that provides a stable living—computer science—and worked hard to land a software engineering job, and for the last seven or so years, I have kept my head down and worked.

While I feel extremely fortunate to be where I am in life currently, I also reflect on the years since college and wonder if I made the right decisions. Hindsight is always twenty-twenty, but I still think about a few defining moments in my post-college career thus far and wonder what could have been if I had made riskier decisions.

Something I’ve come to realize recently is that taking risks is extremely important in life. Without ever taking risks, you limit yourself to only regular decisions and regular decisions yield regular results. I’m not recommending that you go to Vegas and put it all in red, but rather that you take calculated risks. The best calculated risks to identify are the ones that provide you with sizable returns without requiring you to bet the house.

Before taking calculated risks, it’s important to know your goals, for without them you can’t steer the ship in the right direction. This is another epiphany I’ve had recently. Making decisions, significant life decisions, before solidifying what you’re after is putting the cart before the horse — if you don’t know your destination you can’t guarantee that you’re moving closer to where you want to be. Making decisions without goals looks a lot like the following, no man’s land:

You make “progress” in random directions without a unified aim. While you can take risks in this phase it’s ill-advised given that it’s hard to justify the reward: a prize you’re unsure you’re even interested in. What this phase is valuable for is exploration. If you’ve thought about your goals critically, but aren’t sure what you’d like to pursue trying things to find the correct direction to travel in is crucial. Once you do, you’ll most likely move on to the next phase where I currently find myself, the parallel universe:

Now that you know what you’re after, this diagram shows where you are and where you want to be in relation to one another. The problem with this diagram is that it also clearly depicts that these two paths (i.e. the path you’re currently on and the path you’d like to walk) are parallel and will therefore never intersect. Because of this, if you never change what you’re currently doing, you’ll never reach your goal (reread this sentence, it should terrify you). This is where calculated risks must be taken as they’ll help you bridge the gap and reach your goal in the final phase, the long walk:

While it can be daunting to course-correct it’s a required step to crossover from where you are to where you want to be. When taking these risks it’s helpful to consider whether or not a particular decision is a one-way or two-way door. This framework is something I learned from my time at Amazon and I’ve found it particularly helpful when calculating risk. One-way doors are, as the name implies, one way and you should therefore think long and hard about that decision since once it’s made it’s hard or impossible to reverse. Two-way door decisions on the other hand are easily reversible and therefore can be made swiftly. In your situation, consider what kind of decision you’re facing and if it’s a one-way door decision see if there are steps before it that can be made that are two-way doors.

For some things in life, you have to go out on a limb, that’s where the fruit is — you can’t expect outsized returns from regular investments. It’s also imperative to act with urgency as not all doors remain open to you indefinitely. For example, as much as I’d like to believe it, the time for me to become an NBA player (genetics aside) has come and gone. This idea reminds me of a diagram from a previous post of mine:

There are many decisions you’ve made that have landed you at the very place you are today. Similarly, there are many paths ahead of you that you can choose from going forward albeit not all of them will always be available.

Calculate risk and take action when it makes sense to do so. But whatever you do, ensure that throughout life you take risks because ironically, never taking risks is the riskiest thing you can do.

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